Hydrochloric Acid → 1-(3-Iodobenzyl)imidazolidine-2,4-dione

HRID 857130Notes

Reaction equation

HRID 857130 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[CH2:5][NH:6][CH2:7][C:8]([O:10]CC)=O.Cl.[O-:17][C:18]#[N:19].[Na+]>>[I:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[CH2:5][N:6]1[CH2:7][C:8](=[O:10])[NH:19][C:18]1=[O:17]

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 517096Sodium CyanateHCID 21867201Ethyl N-(3-iodobenzyl)glycinate

Product 1

HCID 218670381-(3-Iodobenzyl)imidazolidine-2,4-dioneYield 96.7%

Procedure

Ethyl N-(3-iodobenzyl)glycinate (0.567 g) was treated with 1M HCl (3.9 ml) and sodium cyanate (0.345 g) and then refluxed for 30 min. Concentrated HCl (4.5 ml) was added and the reaction mixture refluxed again for 30 min. The reaction mixture was evaporated under reduced pressure and then triturated with EtOAc (3×20 ml). The combined extracts were dried (Na2SO4) and evaporated under reduced pressure to give the title compound (0.543 g). LCMS RT 2.63 min.

Workup

  1. temperaturerefluxed for 30 min
  2. temperaturethe reaction mixture refluxed again for 30 min
  3. customThe reaction mixture was evaporated under reduced pressure
  4. customtriturated with EtOAc (3×20 ml)
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ccf9d125e2294b11bf4165821723040d
Source dataset
uspto-grants-2006_12
Patent number
US07144908B2

Reaction notes

Loading…